Roy Phillips

Roy Phillips was a Pinkerton agent who was hired by Leander Cephas Whitlock to investigate Gillian Darmody's murder of an innocent young man in 1923 to pass him off as the body of her late son, Jimmy Darmody, as a part of a plot to take over his belongings.

Biography
Roy Phillips worked as a detective for the Pinkerton detective agency, and he was hired by Leander Cephas Whitlock to investigate the murder of Roger McAllister by Gillian Darmody in 1923. Phillips pretended to be the executive of the Piggly Wiggly market chain, and he met with Darmody at her late partner Louis Kaestner's mansion to discuss buying the property. He found it too big for his fictitious wife's tastes, but he asked Darmody to help him in learning about the city. Philips had her pose as his wife at a meeting with a businessman from Evansville, Indiana at an Atlantic City restaurant, and Phillips later told Darmody that he had already divorced his wife, and that he had fallen for her.

The two began an intimate relationship, and Phillips helped Darmody with getting off heroin cold-turkey and changing her ways. Phillips then shot the businessman from Evansville in a parking garage when the businessman angrily confronted him about the merger of their two companies, which cost the businessman lots of money; Phillips gunned him down as he reached into his pocket and told him that he would show him what it felt like to lose everything. Phillips pretended to be in shock, and he made himself look like a killer. As the two of them sat on the staircase of the Darmody mansion, Darmody explained ways to get over murdering someone, and she confessed to the murder of Roger McAllister in the process. Phillips then asked fellow agents if they had heard the confession, and the agents came into the open and acknowledged that they had heard a confession of guilt. Whitlock himself came out of hiding and appeared, and Phillips informed Darmody that he was a Pinkerton agent. Darmody angrily attacked him, but she was restrained and taken to jail.